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This paper will example multiple early 1990s games all named "Perestroika" or imagining "Perestroika" as a bombastic break with the burdens of history, staging this break as either the outcome or process of play. I will examine these games as historical epistemologies of the present, suspended oddly in between the hopeful futurity suggested by the chosen medium of computer game in the early 1990s, and their almost immediate technological obsolescence (no one plays these games now, it is very difficult to make them work on modern computers).